Microwave-assisted synthesis and antibacterial activity of derivatives of 3-[1-(4-fluorobenzyl)-1H-indol-3-yl]-5-(4-fluorobenzylthio)-4H-1,2,4-triazol-4-amine
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Yong-Le Peng
,
Xing-Li Liu
Abstract
Herein, an excellent method for the synthesis of twelve novel Schiff base derivatives containing indole and triazole assisted by microwave irradiation is reported. Compared with the conventional method, the yields increased from 59–84 % to 85–96 % and the reaction time was reduced from 24–30 h to 4–8 min. Moreover, all series of the newly synthesized Schiff bases were evaluated for their antibacterial activity. The values of minimum inhibitory concentration (MIC) and IC50 indicated that many target compounds possessed excellent antibacterial activity against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis.
[1] Akhaja, T. N., & Raval, J. P. (2011). 1,3-Dihydro-2H-indol-2-ones derivatives: Design, synthesis, in vitro antibacterial, antifungal and antitubercular study. European Journal of Medicinal Chemistry, 46, 5573–5579. DOI: 10.1016/j.ejmech.2011.09.023. http://dx.doi.org/10.1016/j.ejmech.2011.09.02310.1016/j.ejmech.2011.09.023Suche in Google Scholar PubMed
[2] Akhaja, T. N., & Raval, J. P. (2012). Design, synthesis, in vitro evaluation of tetrahydropyrimidine-isatin hybrids as potential antibacterial, antifungal and anti-tubercular agents. Chinese Chemical Letters, 23, 446–449. DOI: 10.1016/j.cclet.2012.01.040. http://dx.doi.org/10.1016/j.cclet.2012.01.04010.1016/j.cclet.2012.01.040Suche in Google Scholar
[3] Appukkuttan, P., Mehta, V. P., & Van der Eycken, E. V. (2009). Microwave-assisted cycloaddition reactions. Chemical Society Reviews, 39, 1467–1477. DOI: 10.1039/b815717k. http://dx.doi.org/10.1039/b815717k10.1039/B815717KSuche in Google Scholar PubMed
[4] Bharti, S. K., Nath, G., Tilak, R., & Singh, S. K. (2010). Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2,4-disubstituted thiazole ring. European Journal of Medicinal Chemistry, 45, 651–660. DOI: 10.1016/j.ejmech.2009.11.008. http://dx.doi.org/10.1016/j.ejmech.2009.11.00810.1016/j.ejmech.2009.11.008Suche in Google Scholar PubMed
[5] Burchak, O. N., Le Pihive, E., Maigre, L., Guinchard, X., Bouhours, P., Jolivalt, C., Schneider, D., Maurin, M., Giglione, C., Meinnel, T., Paris, J. M., & Denis, J. N. (2011). Synthesis and evaluation of 1-(1H-indol-3-yl)ethanamine derivatives as new antibacterial agents. Bioorganic & Medicinal Chemistry, 19, 3204–3215. DOI: 10.1016/j.bmc.2011.03.060. http://dx.doi.org/10.1016/j.bmc.2011.03.06010.1016/j.bmc.2011.03.060Suche in Google Scholar PubMed
[6] da Silva, C. M., da Silva, D. L., Modolo, L. V., Alves, R. B., de Resende, M. A., Martins, C. V. B., & de Fátima, Â. (2011). Schiff bases: A short review of their antimicrobial activities. Journal of Advanced Research, 2, 1–8. DOI: 10.1016/j.jare.2010.05.004. http://dx.doi.org/10.1016/j.jare.2010.05.00410.1016/j.jare.2010.05.004Suche in Google Scholar
[7] Eswaran, S., Adhikari, A. V., & Shetty, N. S. (2009). Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety. European Journal of Medicinal Chemistry, 44, 4637–4647. DOI: 10.1016/j.ejmech.2009.06. 031. http://dx.doi.org/10.1016/j.ejmech.2009.06.03110.1016/j.ejmech.2009.06.031Suche in Google Scholar PubMed
[8] Farghaly, A. R. A. H. (2004). Synthesis, reactions and antimicrobial activity of some new indolyl-1,3,4-oxadiazole, triazole and pyrazole derivatives. Journal of the Chinese Chemical Society, 51, 147–156. Suche in Google Scholar
[9] Giske, C. G., & Cornaglia, G. (2010). Supranational surveillance of antimicrobial resistance: The legacy of the last decade and proposals for the future. Drug Resistance Updates, 13, 93–98. DOI: 10.1016/j.drup.2010.08.002. http://dx.doi.org/10.1016/j.drup.2010.08.00210.1016/j.drup.2010.08.002Suche in Google Scholar PubMed
[10] Ju, Y. H., & Varma, R. S. (2005). Microwave-assisted cyclocondensation of hydrazine derivatives with alkyl dihalides or ditosylates in aqueous media: syntheses of pyrazole, pyrazolidine and phthalazine derivatives. Tetrahedron Letters, 46, 6011–6014. DOI: 10.1016/j.tetlet.2005.07.018. http://dx.doi.org/10.1016/j.tetlet.2005.07.01810.1016/j.tetlet.2005.07.018Suche in Google Scholar
[11] Khalil, N. S. A. M. (2010). Efficient synthesis of novel 1,2,4-triazole fused acyclic and 21–28 membered macrocyclic and/or lariat macrocyclic oxaazathia crown compounds with potential antimicrobial activity. European Journal of Medicinal Chemistry, 45, 5265–5277. DOI: 10.1016/j.ejmech.2010.08.046. http://dx.doi.org/10.1016/j.ejmech.2010.08.04610.1016/j.ejmech.2010.08.046Suche in Google Scholar PubMed
[12] Nadal, M., Schuhmacher, M., & Domingo, J. L. (2011). Longterm environmental monitoring of persistent organic pollutants and metals in a chemical/petrochemical area: Human health risks. Environmental Pollution, 159, 1769–1777. DOI: 10.1016/j.envpol.2011.04.007. http://dx.doi.org/10.1016/j.envpol.2011.04.00710.1016/j.envpol.2011.04.007Suche in Google Scholar PubMed
[13] National Committee for Clinical Laboratory Standards (2000). U.S. standard: Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard, 5th ed. M7-A5. Villanova, PA, USA. Suche in Google Scholar
[14] Negm, N. A., Aiad, I. A., & Tawfik, S. M. (2010). Screening for potential antimicrobial activities of some cationic uracil biocides against wide-spreading bacterial strains. Journal of Surfactants and Detergents, 13, 503–511. DOI: 10.1007/s11743-010-1229-0. http://dx.doi.org/10.1007/s11743-010-1229-010.1007/s11743-010-1229-0Suche in Google Scholar
[15] Pardeshi, S., & Bobade, V. D. (2011). Synthesis and biological evaluation of some novel triazol-3-ones as antimicrobial agents. Bioorganic & Medicinal Chemistry Letters, 21, 6559–6562. DOI: 10.1016/j.bmcl.2011.08.049. http://dx.doi.org/10.1016/j.bmcl.2011.08.04910.1016/j.bmcl.2011.08.049Suche in Google Scholar PubMed
[16] Patil, B. S., Krishnamurthy, G., Naik, H. S. B., Latthe, P. R., & Ghate, M. (2010). Synthesis, characterization and antimicrobial studies of 2-(4-methoxy-phenyl)-5-methyl-4-(2-arylsulfanyl-ethyl)-2,4-dihydro-[1,2,4]triaz olo-3-ones and their corresponding sulfones. European Journal of Medicinal Chemistry, 45, 3329–3334. DOI: 10.1016/j.ejmech.2010.04.016. http://dx.doi.org/10.1016/j.ejmech.2010.04.01610.1016/j.ejmech.2010.04.016Suche in Google Scholar PubMed
[17] Reddy, B. V. S., Rajeswari, N., Sarangapani, M., Reddy, G. R., Madan, C., Kumar, K. P., & Rao, M. S. (2011). Iodine-catalyzed conjugate addition of indoles onto en-1,4-dione: A novel synthesis of 3-(1-(1H-indol-3-yl)-2-oxo-2-phenylethyl)indolin-2-ones as antibacterial and antifungal agents. Bioorganic & Medicinal Chemistry Letters, 21, 6510–6514. DOI: 10.1016/j.bmcl.2011.08.075. http://dx.doi.org/10.1016/j.bmcl.2011.08.07510.1016/j.bmcl.2011.08.075Suche in Google Scholar PubMed
[18] Shi, Y., Peng, Y. L., Zhao, Z. G., Li, G. H., & Li, H. R. (2011). Synthesis of new Schiff bases derived from dimers of 4-amino-3-(1-naphthyl)-5-thiomethyl-1,2,4-triazole using microwave irradiation. Journal of Chemical Research, 35, 15–17. DOI: 10.3184/174751911x12964930076647. http://dx.doi.org/10.3184/174751911X1296493007664710.3184/174751911X12964930076647Suche in Google Scholar
[19] Singh, K., Kumar, Y., Puri, P., Kumar, M., & Sharma, C. (2012). Cobalt, nickel, copper and zinc complexes with 1,3-diphenyl-1H-pyrazole-4-carboxaldehyde Schiff bases: Antimicrobial, spectroscopic, thermal and fluorescence studies. European Journal of Medicinal Chemistry, 52, 313–321. DOI: 10.1016/j.ejmech.2012.02.053. http://dx.doi.org/10.1016/j.ejmech.2012.02.05310.1016/j.ejmech.2012.02.053Suche in Google Scholar PubMed
[20] Zhang, H. J., Qin, X., Liu, K., Zhu, D. D., Wang, X. M., & Zhu, H. L. (2011). Synthesis, antibacterial activities and molecular docking studies of Schiff bases derived from N-(2/4-benzaldehyde-amino) phenyl-N-phenylthiourea. Bioorganic & Medicinal Chemistry, 19, 5708–5715. DOI: 10.1016/j.bmc.2011.06.077. http://dx.doi.org/10.1016/j.bmc.2011.06.07710.1016/j.bmc.2011.06.077Suche in Google Scholar PubMed
[21] Zhao, Z. G., Liu, X. L., Liu, L. L., & Li, G. H. (2010). Microwave-assisted synthesis of new steroidal thiosemicarbazones derived from methyl 3-oxocholanate under solventfree conditions. Journal of Chemical Research, 34, 455–458. DOI: 10.3184/030823410x12798092457988. http://dx.doi.org/10.3184/030823410X1279809245798810.3184/030823410X12798092457988Suche in Google Scholar
[22] Zoumpoulakis, P., Camoutsis, C., Pairas, G., Soković, M., Glamočlija, J., Potamitis, C., & Pitsas, A. (2012). Synthesis of novel sulfonamide-1,2,4-triazoles, 1,3,4-thiadiazoles and 1,3,4-oxadiazoles, as potential antibacterial and antifungal agents. Biological evaluation and conformational analysis studies. Bioorganic & Medicinal Chemistry, 20, 1569–1583. DOI: 10.1016/j.bmc.2011.12.031. http://dx.doi.org/10.1016/j.bmc.2011.12.03110.1016/j.bmc.2011.12.031Suche in Google Scholar PubMed
© 2013 Institute of Chemistry, Slovak Academy of Sciences
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- DFT study on [4+2] and [2+2] cycloadditions to [60] fullerene
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Artikel in diesem Heft
- Analytical protocol for investigation of zinc speciation in plant tissue
- Assessment of waxy and non-waxy corn and wheat cultivars as starch substrates for ethanol fermentation
- Effect of quaternary ammonium silane coating on adhesive immobilization of industrial yeasts
- Modeling of supercritical fluid extraction of flavonoids from Calycopteris floribunda leaves
- Determination of limiting current density for different electrodialysis modules
- Dyeing of multiple types of fabrics with a single reactive azo disperse dye
- Physicochemical fractionation of americium, thorium, and uranium in Chernozem soil after sharp temperature change and soil drought
- Ultra-trace determination of Pb(II) and Cd(II) in drinking water and alcoholic beverages using homogeneous liquid-liquid extraction followed by flame atomic absorption spectrometry
- Synthesis, thermal stability, electronic features, and antimicrobial activity of phenolic azo dyes and their Ni(II) and Cu(II) complexes
- Inhibition of copper corrosion in acidic sulphate media by eco-friendly amino acid compound
- Formation of nanostructured polyaniline by dopant-free oxidation of aniline in a water/isopropanol mixture
- Total synthesis of cannabisin F
- Design and synthesis of novel thiopheno-4-thiazolidinylindoles as potent antioxidant and antimicrobial agents
- Microwave-assisted synthesis and antibacterial activity of derivatives of 3-[1-(4-fluorobenzyl)-1H-indol-3-yl]-5-(4-fluorobenzylthio)-4H-1,2,4-triazol-4-amine
- DFT study on [4+2] and [2+2] cycloadditions to [60] fullerene
- Efficient thioacetalisation of carbonyl compounds
- Trimerization of aldehydes with one α-hydrogen catalyzed by sodium hydroxide
